Next Article in Journal
Synthesis and Antibacterial Properties of New 8-Nitrofluoroquinolone Derivatives
Previous Article in Journal
Composition and Enantiomeric Analysis of the Essential Oil of the Fruits and the Leaves of Pistacia vera from Greece
Molecules 2007, 12(5), 1035-1044; doi:10.3390/12051035
Article

Lupane Triterpenoids from Acacia mellifera with Cytotoxic Activity

1
,
1
,
1,* , 3
,
3
 and
1
Received: 7 April 2007 / Revised: 12 May 2007 / Accepted: 14 May 2007 / Published: 15 May 2007
Download PDF [85 KB, uploaded 18 June 2014]

Abstract

Three new pentacyclic triterpenoids: (20R)-3-oxolupan-30-al (1), (20S)-3-oxolupan-30-al (2) and (20R)-28-hydroxylupen-30-al-3-one (3), along with (20S)-3β-hydroxylupan-30-al (4), the latter previously described as a constituent of an epimeric mixture, were isolated from Acacia mellifera. In addition, the known metabolites 30-hydroxylup-20-(29)-en-3-one (5), 30-hydroxylup-20-(29)-en-3β-ol (6), atranorin, methyl 2,4-dihydroxy-3,6 dimethyl benzoate, sitosterol-3β-O-glucoside and linoleic acid were found in the analyzed plant species for the first time. The structures of the new metabolites were elucidated by extensive spectroscopic analyses and their relative stereochemistry was determined by NOESY experiments. The new metabolite 3 exhibited significant cytotoxic activity against the NSCLC-N6 cell line, derived from a human non-small-cell bronchopulmonary carcinoma.
Keywords: Acacia mellifera; lupanes; cytotoxicity; NSCLC-N6 cell line; (20R)-28-hydroxylupen-30-al-3-one; (20R)-3-oxolupan-30-al; (20S)-3-oxolupan-30-al Acacia mellifera; lupanes; cytotoxicity; NSCLC-N6 cell line; (20R)-28-hydroxylupen-30-al-3-one; (20R)-3-oxolupan-30-al; (20S)-3-oxolupan-30-al
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
MDPI and ACS Style

Mutai, C.; Abatis, D.; Vagias, C.; Moreau, D.; Roussakis, C.; Roussis, V. Lupane Triterpenoids from Acacia mellifera with Cytotoxic Activity. Molecules 2007, 12, 1035-1044.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

Cited By

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert